Aspartyl-Proline

Common Name

Aspartyl-Proline Description

Aspartyl-Proline is a dipeptide composed of aspartate and proline. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

Synonyms

Value Source Asp-proHMDB Aspartate proline dipeptideHMDB Aspartate-proline dipeptideHMDB AspartylprolineHMDB D-P DipeptideHMDB DP DipeptideHMDB L-Aspartyl-L-prolineHMDB

Chemical Formlia

C₉H₁₄N₂O₅ Average Molecliar Weight

230.2179 Monoisotopic Molecliar Weight

230.090271568 IUPAC Name

1-(2-amino-3-carboxypropanoyl)pyrrolidine-2-carboxylic acid Traditional Name

1-(2-amino-3-carboxypropanoyl)pyrrolidine-2-carboxylic acid CAS Registry Number

Not Available SMILES

InChI Identifier

InChI Key

UKGGPJNBONZZCM-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

Proline and derivatives

N-acyl-alpha amino acids

Alpha amino acid amides

Pyrrolidine carboxylic acids

N-acylpyrrolidines

Heterocyclic fatty acids

Dicarboxylic acids and derivatives

Tertiary carboxylic acid amides

Amino acids

Azacyclic compounds

Carboxylic acids

Hydrocarbon derivatives

Carbonyl compounds

Monoalkylamines

Organic oxides

Organopnictogen compounds

Substituents

Alpha-dipeptide

N-acyl-alpha amino acid or derivatives

Proline or derivatives

N-acyl-alpha-amino acid

Alpha-amino acid amide

Alpha-amino acid or derivatives

N-acylpyrrolidine

Pyrrolidine carboxylic acid

Pyrrolidine carboxylic acid or derivatives

Heterocyclic fatty acid

Dicarboxylic acid or derivatives

Fatty acyl

Fatty acid

Tertiary carboxylic acid amide

Pyrrolidine

Amino acid

Amino acid or derivatives

Carboxamide group

Carboxylic acid

Azacycle

Organoheterocyclic compound

Organic oxygen compound

Primary aliphatic amine

Organic nitrogen compound

Hydrocarbon derivative

Organic oxide

Carbonyl group

Organopnictogen compound

Amine

Primary amine

Organooxygen compound

Organonitrogen compound

Aliphatic heteromonocyclic compound

Molecliar Framework

Aliphatic heteromonocyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Endogenous

Biofunction

Not Available Application

Not Available Cellliar locations

Not Available Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-3.84Extrapolated

Predicted Properties

Property Value Source Water Solubility32.1 mg/mLALOGPS logP-3.3ALOGPS logP-4ChemAxon logS-0.86ALOGPS pKa (Strongest Acidic)3.1ChemAxon pKa (Strongest Basic)8.52ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area120.93 ŲChemAxon Rotatable Bond Count4ChemAxon Refractivity51.52 m³·mol^-1ChemAxon Polarizability21.39 ųChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Not Available Biological Properties Cellliar Locations

Not Available Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

Not Available KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB28761 Metagene Link

HMDB28761 METLIN ID

Not Available PubChem Compound

Not Available PDB ID

Not Available ChEBI ID

Not Available

Product: MT-DADMe-ImmA

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Titani K, Koide A, Ericsson LH, Kumar S, Hermann J, Wade RD, Walsh KA, Neurath H, Fischer EH: Sequence of the carboxyl-terminal 492 residues of rabbit muscle glycogen phosphorylase including the pyridoxal 5-phosphate binding site. Biochemistry. 1978 Dec 26;17(26):5680-93. [PubMed:728426 ]
2. Li Y, Li X, Wang G: Cloning, expression, isotope labeling, and purification of human antimicrobial peptide LL-37 in Escherichia coli for NMR studies. Protein Expr Purif. 2006 Jun;47(2):498-505. Epub 2005 Nov 14. [PubMed:16325420 ]
3. Matsui S, Srivastava VP, Holt EM, Taylor EW, Stammer CH: Synthesis and conformational analysis of L-aspartylproline and L-aspartyl-2,3-methanoproline propyl esters. Int J Pept Protein Res. 1991 Apr;37(4):306-14. [PubMed:1894445 ]
4. Li BC, Zhang SQ, Dan WB, Chen YQ, Cao P: Expression in Escherichia coli and purification of bioactive antibacterial peptide ABP-CM4 from the Chinese silk worm, Bombyx mori. Biotechnol Lett. 2007 Jul;29(7):1031-6. Epub 2007 Mar 21. [PubMed:17375264 ]
5. Benz R, Francis G, Nakae T, Ferenci T: Investigation of the selectivity of maltoporin channels using mutant LamB proteins: mutations changing the maltodextrin binding site. Biochim Biophys Acta. 1992 Mar 2;1104(2):299-307. [PubMed:1547266 ]
6. Elliott BW Jr, Steiner LA: Amino- and carboxy-terminal sequence of mouse J chain and analysis of tryptic peptides. J Immunol. 1984 Jun;132(6):2968-74. [PubMed:6427330 ]

PMID: 9259015